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ID: ALA293012
Max Phase: Preclinical
Molecular Formula: C25H22O6S
Molecular Weight: 450.51
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: Cc1ccc(C2=C(C(=O)O)C(c3ccc4c(c3)OCO4)Oc3ccc(OC(C)C)cc32)s1
Standard InChI: InChI=1S/C25H22O6S/c1-13(2)30-16-6-8-18-17(11-16)22(21-9-4-14(3)32-21)23(25(26)27)24(31-18)15-5-7-19-20(10-15)29-12-28-19/h4-11,13,24H,12H2,1-3H3,(H,26,27)
Standard InChI Key: FSKVJGRQYIHVTI-UHFFFAOYSA-N
Associated Targets(Human)
EDNRA Tclin Endothelin receptor ET-A (5008 Activities)
EDNRB Tclin Endothelin receptor ET-B (1928 Activities)
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Associated Targets(non-human)
Ednra Endothelin receptor ET-A (1158 Activities)
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EDNRB Endothelin receptor ET-B (471 Activities)
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Molecule Features
| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Properties
| Molecular Weight: 450.51 | Molecular Weight (Monoisotopic): 450.1137 | AlogP: 5.59 | #Rotatable Bonds: 5 |
| Polar Surface Area: 74.22 | Molecular Species: ACID | HBA: 6 | HBD: 1 |
| #RO5 Violations: 1 | HBA (Lipinski): 6 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: 2.59 | CX Basic pKa: | CX LogP: 5.63 | CX LogD: 2.12 |
| Aromatic Rings: 3 | Heavy Atoms: 32 | QED Weighted: 0.55 | Np Likeness Score: -0.25 |
References
| 1. Ishizuka N, Matsumura K, Sakai K, Fujimoto M, Mihara S, Yamamori T.. (2002) Structure-activity relationships of a novel class of endothelin-A receptor antagonists and discovery of potent and selective receptor antagonist, 2-(benzo[1,3]dioxol-5-yl)-6-isopropyloxy-4-(4-methoxyphenyl)-2H-chromene-3-carboxylic acid (S-1255). 1. Study on structure-activity relationships and basic structure crucial for ET(A) antagonism., 45 (10): [PMID:11985472] [10.1021/jm010382z] |
| 2. Boss C, Bolli MH, Gatfield J.. (2016) From bosentan (Tracleer®) to macitentan (Opsumit®): The medicinal chemistry perspective., 26 (15): [PMID:27321813] [10.1016/j.bmcl.2016.06.014] |
Source
Source(1):